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Triphenylphosphine → Ethyl 3-{4-[2-(4-chlorophenyl)ethoxy]phenyl}-3-ethoxypropionate

HRID 1515080
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1515080
[CH2:1]([O:3][CH:4]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26]O)=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][O:17][C:14]2[CH:13]=[CH:12][C:11]([CH:4]([O:3][CH2:1][CH3:2])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:16][CH:15]=2)=[CH:21][CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 74647p-Chlorophenethylic alcoholHCID 66777355Diethylazodicarboxylate tolueneHCID 67058135Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate

Produkt 1

HCID 67058050Ethyl 3-{4-[2-(4-chlorophenyl)ethoxy]phenyl}-3-ethoxypropionateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate (100 mg, 0.420 mmol) produced in Example 1 (1C) and 2-(4-chlorophenyl)ethanol (99 mg, 0.630 mmol) were dissolved in tetrahydrofuran (10 mL), and triphenylphosphine (178 mg, 0.680 mmol) and a 40% diethyl azodicarboxylate toluene solution (309 μL, 0.680 mmol) were added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 50° C. for 4 hours. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound was obtained as a yellow oily substance (151 mg, yield: 95%).

Aufarbeitung

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound
  4. customwas obtained as a yellow oily substance (151 mg, yield: 95%)

Quellen und Nachweise

ORD-Eintrag
ord-cf0707538b08479086f077ff5d25f377
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222281B2

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